Intramolecular General Acid Catalysis of Intramolecular Nucleophilic Catalysis of the Hydrolysis of a Phosphate Diester
The dianion (8) of bis-2-carboxyphenyl phosphate (half-life 10.2 min at 39 deg C) is hydrolysed ca. 1E10 times faster than diphenyl phosphate.The reaction is accounted for in terms of intramolecular general acid catalysis by the ortho-CO2H of one salicyl group of the breakdown of the penta-covalent intermediate formed by the addition to phosphorus of the carboxylate group of the other.The general acid catalysis part of the process is unexpectedly inefficient.
Abell, Katherine W. Y.,Kirby, Anthony J.
p. 1171 - 1174
(2007/10/02)
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